A clean and efficient synthesis of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles using silver tetrafluoroborate as a fluorodesulfurization reagent

5-Ethylthio-6,6,7,7-tetramethyl substituted 4-oxa-1,3-diazabicyclo[3.2.0]hept-2-enes undergo fluorodesulfurization with silver tetrafluoroborate to furnish high yields of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles. Ethylthio substituted 1,2,4-triaza- and 1,3-diaza-bicyclo[...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2000-10, Vol.106 (1), p.83-86
Main Authors: Hemming, Karl, Morgan, Dexter T., Smalley, Robert K.
Format: Article
Language:English
Subjects:
1,2,4-Oxadiazoles
1,2,4-Triazoles
Fluoroalkyl substituted heterocycles
Fluorodesulfurization
Silver tetrafluoroborate
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Summary:5-Ethylthio-6,6,7,7-tetramethyl substituted 4-oxa-1,3-diazabicyclo[3.2.0]hept-2-enes undergo fluorodesulfurization with silver tetrafluoroborate to furnish high yields of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles. Ethylthio substituted 1,2,4-triaza- and 1,3-diaza-bicyclo[3.2.0]hept-2-enes behave in a similar fashion to yield 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-triazoles and imidazoles, respectively.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(00)00313-4